Preparation of aliphatic poly(thioester) by the lipase-catalyzed direct polycondensation of 11-mercaptoundecanoic acid |
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Authors: | Kato Makoto Toshima Kazunobu Matsumura Shuichi |
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Affiliation: | Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan. |
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Abstract: | An aliphatic polythioester was enzymatically prepared by the direct polycondensation of mercaptoalkanoic acid using immobilized lipase of Candida antarctica (lipase CA) in bulk. The commercially available 11-mercaptoundecanoic acid was polymerized by lipase CA in bulk in the presence of molecular sieves 4A as a water absorbent at 110 degrees C for 48 h to produce poly(11-mercaptoundecanoate) with an M(w) of 34 000 in high yield. The 104.5 degrees C melting temperature (T(m)) of poly(11-mercaptoundecanoate) was about 20 degrees C higher than that of the corresponding polyoxyester, poly(11-hydroxyundecanoate). The polythioester was readily transformed by lipase into the corresponding cyclic oligomers mainly consisting of the dimer, which were readily repolymerized by the ring-opening polymerization using lipase as a sustainable chemical recycling. |
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